Cow Key Holidays

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Top hotels in Cow Key

Beachside Resort & Residences
Beachside Resort & Residences
3.5 out of 5
3841 N Roosevelt Blvd, Key West, FL
Fully refundableReserve now, pay when you stay
The price is S$452 per night from 14 Apr to 15 Apr
S$452
includes taxes & fees
14 Apr - 15 Apr
8.2/10 Very Good! (1,012 reviews)
"Front desk was some of the best customer service we ever had."

Reviewed on 31 Mar,2025

Beachside Resort & Residences
Southernmost Beach Resort
Southernmost Beach Resort
4 out of 5
1319 Duval Street, Key West, FL
Fully refundable
The price is S$755 per night from 1 Apr to 2 Apr
S$755
includes taxes & fees
1 Apr - 2 Apr
8.6/10 Excellent! (2,368 reviews)
"Less than luxurious for the price. Handy for Duval. A high end motel that does everything “ok”."

Reviewed on 30 Mar,2025

Southernmost Beach Resort
Margaritaville Beach House Key West
Margaritaville Beach House Key West
4 out of 5
2001 South Roosevelt Boulevard, Key West, FL
Fully refundableReserve now, pay when you stay
The price is S$569 per night from 1 May to 2 May
S$569
includes taxes & fees
1 May - 2 May
8.6/10 Excellent! (1,713 reviews)
"Stay was great. Staff very nice, helpful. Shuttle to/from airport so convenient. Hotel very close to airport. Shuttle into town and back great as well. Exterior grounds well maintained. Rented 2bd room suite with 1.5 bath. Would be nice if had another shower/tub esp with 5 ppl. Rooms clean, modernized ..."

Reviewed on 31 Mar,2025

Margaritaville Beach House Key West
See all 3,187 properties in Cow Key
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much does a Cow Key holiday package cost?
Offering great value package deals on Expedia, you’ll be pleasantly surprised at how much a holiday to Cow Key costs! Expedia’s packages make travel planning easier and your savings go further.
What are the cheapest months to go to Cow Key?
You’re likely to find reduced prices and greater availability in January, February and August. Take a look at our cheap Cow Key holiday packages and you could score some excellent off-season deals.
How many days is enough for Cow Key?
Generally, a handful of days is enough to tick off the major sights during your Cow Key holiday. But if you prefer to have some time to rest or take day tours, consider extending your itinerary.
How to find the best Cow Key package deals?
Use Expedia’s filters to help you find some unbeatable Cow Key package deals. When you begin your search, just set your maximum budget and then sort the results by “Price: low to high.” If you’re looking to save, plan your trip for midweek, or look for Cow Key package deals in the low season. Play around with your travel dates and you may score even better discounts. As a rule of thumb, it’s typically best to lock in your holiday package as early as possible.
Is it cheaper to book a Cow Key holiday as a package?
An Expedia holiday package could land you significant savings when compared to arranging flights and stays individually. Better still, you can customise your Cow Key escape to match your exact needs. Choose your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.
When to book a holiday package to Cow Key?
If you’ve got your Cow Key travel dates confirmed, book as soon as you can to score some outstanding deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spontaneous adventures? Our last-minute deals are ideal for jetting off on a whim.
How to plan a trip to Cow Key?

  1. Choose the ideal time to travel: Your schedule, preferred season and the type of weather you like can all influence your decision on when to go to Cow Key.
  2. Calculate your budget: Ensure you have enough money to pay for everything from dining out and transportation to experiences and flights. Your accommodation will likely be the biggest expense during your trip to Cow Key.
  3. Decide how long to go for: Now that you know more about Cow Key, you can work out the ideal length of your break. Create a draft plan and give yourself enough time to cover everything you want to do.
  4. Bundle your bookings: With your travel dates in order, you can combine your hotels, flights, car rental and more into a customised Cow Key holiday package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.